US4447609A - Method of preparing 2-alkoxy-4-aminopyrimidines - Google Patents

Method of preparing 2-alkoxy-4-aminopyrimidines Download PDF

Info

Publication number: US4447609A
Authority: US; United States
Prior art keywords: amino; alkyl; carbon atoms; alcohol; hydrogen
Prior art date: 1981-03-25
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

US06/358,973

Other languages

English (en)

Inventor

Hermann Peeters

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Dynamit Nobel AG

Original Assignee

Dynamit Nobel AG

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1981-03-25

Filing date

1982-03-17

Publication date

1984-05-08

1982-03-17 Application filed by Dynamit Nobel AG filed Critical Dynamit Nobel AG

1982-03-17 Assigned to DYNAMIT NOBEL AG; A GERMAN CORP. reassignment DYNAMIT NOBEL AG; A GERMAN CORP. ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: PEETERS, HERMANN

1984-05-08 Application granted granted Critical

1984-05-08 Publication of US4447609A publication Critical patent/US4447609A/en

2002-03-17 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 19
238000006243 chemical reaction Methods 0.000 claims abstract description 11
125000000217 alkyl group Chemical group 0.000 claims description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
125000004432 carbon atom Chemical group C* 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
239000002585 base Substances 0.000 claims description 5
239000002904 solvent Substances 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
239000003513 alkali Substances 0.000 claims description 2
238000009835 boiling Methods 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
CECXEJLCMCWWPD-UHFFFAOYSA-N 4-amino-5-methylsulfanylpyrimidine-2-carboxylic acid Chemical compound CSC1=CN=C(C(O)=O)N=C1N CECXEJLCMCWWPD-UHFFFAOYSA-N 0.000 claims 3
229910052784 alkaline earth metal Inorganic materials 0.000 claims 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
150000002431 hydrogen Chemical group 0.000 claims 2
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
150000001342 alkaline earth metals Chemical class 0.000 claims 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
239000011541 reaction mixture Substances 0.000 claims 1
JFBBHFVRALBIAT-UHFFFAOYSA-N 2-(4-aminopyrimidin-2-yl)sulfanylacetic acid Chemical class NC1=CC=NC(SCC(O)=O)=N1 JFBBHFVRALBIAT-UHFFFAOYSA-N 0.000 abstract description 9
150000001298 alcohols Chemical class 0.000 abstract description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
DHYLZDVDOQLEAQ-UHFFFAOYSA-N 2-O-methylcytosine Chemical group COC1=NC=CC(N)=N1 DHYLZDVDOQLEAQ-UHFFFAOYSA-N 0.000 description 5
239000000047 product Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 description 3
239000000203 mixture Substances 0.000 description 3
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 2
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
BTTNYQZNBZNDOR-UHFFFAOYSA-N 2,4-dichloropyrimidine Chemical compound ClC1=CC=NC(Cl)=N1 BTTNYQZNBZNDOR-UHFFFAOYSA-N 0.000 description 1
KEVRHVMWBKFGLO-UHFFFAOYSA-N 2,4-dimethoxypyrimidine Chemical compound COC1=CC=NC(OC)=N1 KEVRHVMWBKFGLO-UHFFFAOYSA-N 0.000 description 1
XQSRBEMMGAUIGH-UHFFFAOYSA-N 2-(4-amino-5-benzylpyrimidin-2-yl)sulfanylacetic acid Chemical compound NC1=NC(SCC(O)=O)=NC=C1CC1=CC=CC=C1 XQSRBEMMGAUIGH-UHFFFAOYSA-N 0.000 description 1
OTMIDKVJSMTPJS-UHFFFAOYSA-N 2-(4-amino-5-methylpyrimidin-2-yl)sulfanylacetic acid Chemical compound CC1=CN=C(SCC(O)=O)N=C1N OTMIDKVJSMTPJS-UHFFFAOYSA-N 0.000 description 1
WMHZORSBJYCOPW-UHFFFAOYSA-N 2-[4-amino-5-(methoxymethyl)pyrimidin-2-yl]sulfanylacetic acid Chemical compound COCC1=CN=C(SCC(O)=O)N=C1N WMHZORSBJYCOPW-UHFFFAOYSA-N 0.000 description 1
LPBDZVNGCNTELM-UHFFFAOYSA-N 2-chloropyrimidin-4-amine Chemical compound NC1=CC=NC(Cl)=N1 LPBDZVNGCNTELM-UHFFFAOYSA-N 0.000 description 1
PAILBNDUFZARQN-UHFFFAOYSA-N 2-ethoxypyrimidin-4-amine Chemical compound CCOC1=NC=CC(N)=N1 PAILBNDUFZARQN-UHFFFAOYSA-N 0.000 description 1
XSUSJNAPTDZBTE-UHFFFAOYSA-N 2-methoxy-5-(methoxymethyl)pyrimidin-4-amine Chemical compound COCC1=CN=C(OC)N=C1N XSUSJNAPTDZBTE-UHFFFAOYSA-N 0.000 description 1
GAUNWPNZBQOHGF-UHFFFAOYSA-N 2-methoxy-5-methylpyrimidin-4-amine Chemical compound COC1=NC=C(C)C(N)=N1 GAUNWPNZBQOHGF-UHFFFAOYSA-N 0.000 description 1
GEOLQZUEOKOGAN-UHFFFAOYSA-N 5-benzyl-2-methoxypyrimidin-4-amine Chemical compound NC1=NC(OC)=NC=C1CC1=CC=CC=C1 GEOLQZUEOKOGAN-UHFFFAOYSA-N 0.000 description 1
DCPSTSVLRXOYGS-UHFFFAOYSA-N 6-amino-1h-pyrimidine-2-thione Chemical class NC1=CC=NC(S)=N1 DCPSTSVLRXOYGS-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
229940106681 chloroacetic acid Drugs 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
229940104302 cytosine Drugs 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
MBMGMEMKHNEBGI-UHFFFAOYSA-N ethyl 4-amino-2-methoxypyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(OC)N=C1N MBMGMEMKHNEBGI-UHFFFAOYSA-N 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
-1 lithium aluminum hydride Chemical compound 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
VBPUWWGCJVKSNP-UHFFFAOYSA-N methyl 2-(4-aminopyrimidin-2-yl)sulfanylacetate Chemical compound COC(=O)CSC1=NC=CC(N)=N1 VBPUWWGCJVKSNP-UHFFFAOYSA-N 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
125000003367 polycyclic group Chemical group 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
101150035983 str1 gene Proteins 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000017105 transposition Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine

Definitions

This invention relates to a process for preparing 2-alkoxy-4-aminopyrimidine compounds.
the synthesis of 4-amino-2-alkoxypyrimidines has hitherto been expensive.
the unsubstituted 4-amino-2-alkoxypyrimidine is formed of 2,4-dichloropyrimidine by transposition with ammonia and further reaction of the 4-amino-2-chloropyrimidine with alkali methylate, whereupon an isomer mixture is formed which can be separated only at great expense (J. Amer. Chem. Soc. 52 (1930) 1152; C.A. 52, 6360 b), and by the hydrogenation of the difficultly obtainable 4-amino-6-chloro-2-alkoxypyrimidine (Monatsheft Chem.
the object of the present invention was to synthesize 2-alkoxypyrimidines in a high yield by a simple reaction from easily available and inexpensive starting products. Expensive and complex processes, such as isomer separation, were to be avoided.
R' has the same meaning as in formula 1.
the process delivers the products in high purity and yield.
the 4-amino-2-carboxymethylthiopyrimidines of formula 2 are easily obtained by the reaction of 4-amino-2-mercaptopyrimidines with chloroacetic acid or chloroacetic acid esters (J. Biol. Chem. 177 (1949) 357).
a 4-amino-2-carboxymethylthiopyrimidine (formula 2), in which the group --COOH is used very preferentially, and also preferentially --COOCH 3 and COOC 2 H 5 , as the carboxy group, is reacted with an alcohol in the presence of a base.
the alcohol is generally used in an excess with respect to the 4-amino-2-carboxymethylthiopyrimidine and serves as a solvent or dispersant; the minimum amount of alcohol is generally determined by the stirrability of the reaction solution, but the amount can be reduced, if desired, to about 2 moles per mole of 4-amino-2-carboxymethylthio compound of formula 2.
the concentration of the reaction solution should be as great as possible.
Preferred alcohols are methanol, ethanol, propanol and butanol.
the alcoholate corresponding to the alcohol is preferred as the base, advantageously sodium alcoholate or potassium alcoholate, but other alcoholates can be used, such as alkaline earth alcoholates for example.
Other suitable bases are especially the alkali hydroxides or, in some cases, alkaline earth hydroxides, alkaline earth oxides, or salts of weak acids, such as carbonates for example.
the amount of alcohol will be from 2 to 20, preferably 2 to 10 moles per mole of 4-amino-2-carboxymethylthiopyrimidine and 1 to 20, preferably 2 to 10, moles per mole of 4-amino-2-alkoxycarbonylmethylthiopyrimidine.
the reaction requires elevated temperatures.
the preferred temperature is the boiling point of the solvent, although even higher temperatures of up to about 150° C. are possible under a slight excess pressure.
the reaction time amounts generally to 1 to 10 hours.
the poorly water-soluble 4-amino-2-methoxypyrimidine can be precipitated by the addition of water after the reaction has ended and the methanol has been distilled out, and can be separated from the water-soluble components.
4-Amino-2-alkoxypyrimidines are starting products, for example for pharmaceutically active sulfonamides and for cytosine and cytosine derivatives.

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Plural Heterocyclic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

US06/358,973 1981-03-25 1982-03-17 Method of preparing 2-alkoxy-4-aminopyrimidines Expired - Fee Related US4447609A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE3111613		1981-03-25
DE19813111613 DE3111613A1 (de)	1981-03-25	1981-03-25	Verfahren zur herstellung von 2-alkoxy-4-aminopyrimidinen

Publications (1)

Publication Number	Publication Date
US4447609A true US4447609A (en)	1984-05-08

Family

ID=6128172

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
US06/358,973 Expired - Fee Related US4447609A (en)	1981-03-25	1982-03-17	Method of preparing 2-alkoxy-4-aminopyrimidines

Country Status (5)

Country	Link
US (1)	US4447609A (de)
EP (1)	EP0061019B1 (de)
JP (1)	JPS57169470A (de)
AT (1)	ATE10936T1 (de)
DE (2)	DE3111613A1 (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7138404B2 (en)	2001-05-23	2006-11-21	Hoffmann-La Roche Inc.	4-aminopyrimidine derivatives

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3504895A1 (de) *	1985-02-13	1986-08-14	Basf Ag, 6700 Ludwigshafen	4-aminopyrimidine und diese enthaltende fungizide

Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4188484A (en) *	1976-03-17	1980-02-12	L'Instituto Farmaceutico S.p.A.	(2-Pyrimidinyl-thio)-alkanoic acid amides and their preparation

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1466177A (en) *	1973-03-23	1977-03-02	Sandoz Ltd	4-hydroxy-pyrimidine derivatives

1981
- 1981-03-25 DE DE19813111613 patent/DE3111613A1/de not_active Withdrawn
1982
- 1982-02-26 AT AT82101488T patent/ATE10936T1/de not_active IP Right Cessation
- 1982-02-26 DE DE8282101488T patent/DE3261662D1/de not_active Expired
- 1982-02-26 EP EP82101488A patent/EP0061019B1/de not_active Expired
- 1982-03-17 US US06/358,973 patent/US4447609A/en not_active Expired - Fee Related
- 1982-03-25 JP JP57046467A patent/JPS57169470A/ja active Pending

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4188484A (en) *	1976-03-17	1980-02-12	L'Instituto Farmaceutico S.p.A.	(2-Pyrimidinyl-thio)-alkanoic acid amides and their preparation

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7138404B2 (en)	2001-05-23	2006-11-21	Hoffmann-La Roche Inc.	4-aminopyrimidine derivatives

Also Published As

Publication number	Publication date
EP0061019B1 (de)	1984-12-27
JPS57169470A (en)	1982-10-19
EP0061019A1 (de)	1982-09-29
DE3111613A1 (de)	1982-10-07
DE3261662D1 (en)	1985-02-07
ATE10936T1 (de)	1985-01-15

Legal Events

Date	Code	Title	Description
1982-03-17	AS	Assignment	Owner name: DYNAMIT NOBEL AG; HA PATENTE 5210 TROISDORF BEZ. Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:PEETERS, HERMANN;REEL/FRAME:003982/0079 Effective date: 19820311
1987-12-08	REMI	Maintenance fee reminder mailed
1988-05-08	LAPS	Lapse for failure to pay maintenance fees
1988-05-08	STCH	Information on status: patent discontinuation	Free format text: PATENT EXPIRED DUE TO NONPAYMENT OF MAINTENANCE FEES UNDER 37 CFR 1.362
1988-07-26	FP	Lapsed due to failure to pay maintenance fee	Effective date: 19880508

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US4447609A - Method of preparing 2-alkoxy-4-aminopyrimidines - Google Patents

Info

Links

Classifications

Definitions

Landscapes

Applications Claiming Priority (2)

Publications (1)

Family

ID=6128172

Family Applications (1)

Country Status (5)

Cited By (1)

Families Citing this family (1)

Citations (1)

Family Cites Families (1)

Patent Citations (1)

Cited By (1)

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